Zhao Penggang, Li Lili, Shi Fang, Su Yingpeng, Lv Tinghong, Huo Xing, Wang Xiaolei
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. China.
Department State Key Laboratory of Applied Organic Chemistry, Department of Chemistry Institution, Lanzhou University, Lanzhou 730000, P. R. China.
Org Lett. 2024 Jun 7;26(22):4711-4715. doi: 10.1021/acs.orglett.4c01491. Epub 2024 May 29.
The Catellani reaction offers an opportunity to address multiple chemical bonds in a single pot. However, it is still quite a challenge to construct fully substituted olefins via this strategy, especially in electron-rich, unstable, and highly functionalized glycals. Herein we report the first palladium-catalyzed Catellani reaction for the direct preparation of 1,2-disubstituted C-aryl glycosides from easily available 2-iodoglycals, bromoaryl, and alkene/alkyne substrates. This transformation exhibits a wide substrate scope, accommodating diverse functional groups and intricate molecular frameworks. This innovative reactivity offers an efficient pathway to valuable 1,2-disubstituted carbohydrate analogues and molecular building blocks, facilitating novel strategic bond disconnections and broadening the reactivity landscape of palladium catalysis.
卡特拉尼反应提供了在一锅反应中构建多个化学键的机会。然而，通过这种策略构建完全取代的烯烃仍然是一项相当大的挑战，尤其是在富电子、不稳定且高度官能化的糖烯中。在此，我们报道了首例钯催化的卡特拉尼反应，该反应可从易于获得的2-碘糖烯、溴代芳烃和烯烃/炔烃底物直接制备1,2-二取代的C-芳基糖苷。这种转化具有广泛的底物范围，能够容纳各种官能团和复杂的分子骨架。这种创新的反应性为制备有价值的1,2-二取代碳水化合物类似物和分子构件提供了一条有效途径，有助于实现新颖的策略性键断裂，并拓宽钯催化的反应范围。
